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EP1531927B1 - Procede de preparation de microcapsules aromatiques ou parfumees - Google Patents

Procede de preparation de microcapsules aromatiques ou parfumees Download PDF

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Publication number
EP1531927B1
EP1531927B1 EP03787967A EP03787967A EP1531927B1 EP 1531927 B1 EP1531927 B1 EP 1531927B1 EP 03787967 A EP03787967 A EP 03787967A EP 03787967 A EP03787967 A EP 03787967A EP 1531927 B1 EP1531927 B1 EP 1531927B1
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EP
European Patent Office
Prior art keywords
protein
microcapsules
process according
hardening agent
plant extract
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP03787967A
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German (de)
English (en)
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EP1531927A1 (fr
Inventor
Anandaraman Subramaniam
Anne Reilly
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Firmenich SA
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Firmenich SA
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11—Encapsulated compositions
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
    • A23L27/72—Encapsulation
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P10/00—Shaping or working of foodstuffs characterised by the products
    • A23P10/30—Encapsulation of particles, e.g. foodstuff additives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0208—Tissues; Wipes; Patches
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/06—Making microcapsules or microballoons by phase separation
    • B01J13/10—Complex coacervation, i.e. interaction of oppositely charged particles
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
    • Y10T428/2984—Microcapsule with fluid core [includes liposome]

Definitions

  • the present invention relates to the perfume and flavor industry. It relates more particularly to a coacervation process for the preparation of microcapsules encapsulating a hydrophobic flavor or fragrance ingredient or composition, the process being characterized by the use of a novel and advantageous hardening agent containing a plant extract rich in phenolic compounds.
  • Encapsulation is a term easily used by the food, flavor and fragrance industry.
  • the processes employed for encapsulation may include dehydration techniques such as spray-drying or drum drying, spray chilling, extrusion, mechanical coating or coacervation.
  • Coacervation also called aqueous phase separation, is a very well known technique for encapsulating hydrophobic liquids.
  • a coacervation process allows to provide oil-containing microscopic capsules, the encapsulating material being a gelled hydrophilic colloid that is impervious to the oil and deposited evenly and densely about the oil as nucleus.
  • the encapsulating colloid material is a protein which may be complexed with another colloid having an opposite electric charge.
  • the coacervation process essentially involves an aqueous protein solution which is manipulated by changing the physico-chemical environment (dilution and/or adjustment of pH) to result in phase separation of the protein from the solution to varying degrees depending on the molecular weight of the protein, its iso electric point and compatibility with solvents.
  • a coacervation process can be "simple" or "complex".
  • the former designation is employed when a single protein is used to form a capsule wall as phase separation is taking place.
  • the latter term designates the use of a second oppositely charged non-protein polymer to bring about the phase separation.
  • Complex coacervation method is widely practiced in commercial processes and has been well described in the literature. In particular, US 2,800,457 and US 2,800,458 disclose complex coacervation in a very detailed manner.
  • a coacervation process comprises four basic steps consisting in respectively emulsification, coacervation, wall formation and wall hardening. Therefore, a dispersion of oil droplets in a solution of at least one colloid material is subjected to dilution or pH adjustment to form oil-droplet containing capsules (coacervation). The colloid is further gelled (wall formation) and is finally hardened and water-insolubilized to a point where the capsules are highly resistant to heat and moisture. More particularly, the hardening step consists in cross-linking the colloidal coating present on the emulsified oil droplets.
  • the cross-linking of a protein is critical in encapsulation employing protein and is conventionally performed by the use of an aldehyde such as formaldehyde or glutaraldehyde.
  • an aldehyde such as formaldehyde or glutaraldehyde.
  • the latter compounds present the drawback of being toxic and they cannot be used in the production of microcapsules to be incorporated in foodstuffs.
  • glutaraldehyde which is disclosed as mostly used in coacervation processes, is a hazardous chemical to handle which is moreover not permitted for applications outside the United States.
  • the present invention offers a novel solution to the above-mentioned problems by providing a coacervation process which may be of simple or complex type, and which uses as a hardening agent, i.e. as an agent capable of insolubilizing the protein wall, a plant extract presenting the particularity of being rich in phenolic compounds.
  • a hardening agent i.e. as an agent capable of insolubilizing the protein wall
  • This novel cross-linking agent unexpectedly proved to he very efficient and easy to handle.
  • it is advantageously not submitted to any kind of restriction from a legal point of view.
  • Phenolic compounds have been described in US 3,965,033 and US 3,803,045 as being useful in a coacervation process. However, in the processes disclosed in those documents, such compounds are added at a stage preceding the hardening step and the cross-linking is carried out with conventional hardening agents such as formaldehyde, acetaldehyde or glutaraldehyde.
  • the invention relates to a coacervation encapsulation process, comprising the basic steps of emulsification or dispersion of a hydrophobic core material in a protein solution, coacervation, wall formation by cooling the coacervate, hardening and finally stirring.
  • This process is characterized by the fact that the hardening step is carried out by means of a plant extract rich in phenolic compounds.
  • the invention also relates to the microcapsules that are produced by this process.
  • These microcapsules have gelled walls of a high molecular weight protein which at least partially surround cores of hydrophobic material, wherein the gelled walls are cross-linked by means of a hardening agent containing at least one plant extract comprising substituted or unsubstituted phenolic compounds.
  • the invention also relates to a method for insolubilizing proteins in water by adding at least one plant extract comprising substituted or unsubstituted phenolic compounds to a protein based coacervate wherein the extract is present in an amount sufficient to harden at least a portion of the protein of the coacervate to render it insoluble.
  • the invention is thus provided by a process for the preparation of microcapsules comprising a hydrophobic core material, which process comprises the steps of: a) emulsifying or dispersing a hydrophobic liquid, a solid suspended in a hydrophobic liquid or a solid into a solution of at least one high molecular weight protein ; b) subjecting the emulsion or dispersion obtained in step a) to water dilution and/or pH adjustment to achieve coacervation ; c) cooling the coacervate formed from step b) to provide wall formation of microcapsules ; d) adding at a temperature of between 15 and 30°C a hardening agent to the coacervate to cross-link the wall formed; and e) agitating the mixture for at least 48 h to finish the cross-linking reaction.
  • This process is characterized in that the hardening agent used in step d) contains at least one plant extract comprising substituted or unsubstituted phenolic compounds.
  • high molecular weight protein we mean here a protein with a molecular weight typically comprised between 40000 and 100000.
  • core material encompass hydrophobic liquid materials which are usually subjected to encapsulation by coacervation, as well as solids or solids suspended in a hydrophobic liquid.
  • the plant extract used in the process according to the invention constitutes a novel agent for insolubilizing the protein wall of an encapsulated hydrophobic core material, prepared by coacervation.
  • Cross-linking of a protein is critical for efficiency of the protein-encapsulated core, in particular for its thermostability. If a protein wall is not cross-linked, the delivery system will not perform as desired.
  • the new hardening agent used according to the invention and consisting of at least one plant extract characterized by the fact that it comprises unsubstituted or substituted phenolic compounds unexpectedly proved to efficiently cross-link a protein wall formed after gelation.
  • the delivery systems provided by the process here-described turned out to show a very interesting slow-release of the core material there-encapsulated, compared with traditional systems cross-linked with glutaraldehyde. Moreover, the cross-linked walls of the microcapsules present a good thermostability.
  • the novel hardening agent provided by the present invention presents the advantage of being non hazardous to handle, of low cost, and it does not require rigorously controlled conditions in the process. Other advantages of the invention will appear further in the description, as well as in the examples below.
  • plant extract it is meant here a botanical extract, an herbal extract or yet a wood extract.
  • botanical extracts include for instance oak bark extract, olive water or even cashew nut shell liquid.
  • Tea extract is another example of a plant extract suitable for the purpose of the invention. All these extracts comprise a certain amount of substituted or unsubstituted phenolic compounds, i.e. phenols, their homologues, or substituted phenols such as vanillin, quinones or polyphenols for instance.
  • a liquid smoke also referred to as pyroligneous acid.
  • a liquid smoke also referred to as pyroligneous acid.
  • This material is originally extracted from wood, preferably birch wood. It is described by S. Arctander in Flavor and Fragrance Chemicals, Montclair, New Jersey, 1969, ref. No 2780 , as being a flavor ingredient, useful in the flavoring of meats, fishes and other preserves, and to a lesser extent in flavor compositions for imitation of caramel, butterscotch, rum, vanilla, etc. in tobacco flavoring.
  • Pyroligneous acid extract is further mentioned as being used as "smoke" flavor in products such as meat and fish.
  • This extract comprises, in particular compounds such as guaiacol, 4-methyl guaiacol, 4-ethyl guaiacol, 4-propyl guaiacol, vanillin, 4-(2-propio) vanillone, 4-(1-propio) vanillone, aceto vanillone, eugenol, E-isoeugenol, Z-isoeugenol, syringol, 4-methyl syringol, 4-ethyl syringol, 4-propyl syringol, syringaldehyde, 4-(2-propio)-syringone, 4-(1-propio)-syringone, 4-(2-propenyl) syringol, E-4(1-propenyl) syringol, Z-4(1-propenyl) syringol and acetosyringol.
  • compounds such as guaiacol
  • the organoleptic characteristics of the hydrophobic core encapsulated in particular its flavor in the case of a flavor oil, are advantageously not altered.
  • pyroligneous acid possesses itself flavoring properties as mentioned in reference text books such as that of S. Arctander, it turned out that the smoke flavor is not perceived in the final delivery system cross-linked with the ingredient. This advantage is quite unexpected given that liquid smoke is disclosed as being very strong and hard to mask.
  • the plant extract used for the cross-linking of the protein may be used in conjunction with tannic acid.
  • the hardening agent is used in proportions varying between 0.5 to 2.8% by weight relative to the weight of protein used, on a dry weight basis.
  • the process of the invention starts with the emulsification or dispersion of a hydrophobic liquid, a solid suspended in a hydrophobic liquid or a solid, into a protein solution.
  • both simple and complex coacervation can be performed within the frame of the present invention.
  • the former method involves the addition of a non-solvent or another chemical that competes for solubility with protein, resulting in a protein rich coacervate phase.
  • the complex coacervation process employs the addition of a second oppositely charged polymer solution to neutralize the charges of the protein molecules, resulting in a coacervate with a neutral polymer-polymer complex.
  • the mixture may be made by forming an aqueous solution of protein, emulsifying the core material therein, and mixing the emulsion with an aqueous solution of anionic polymer, or the two solutions may be made and mixed and the core material emulsified therein.
  • Any anionic polymer that reacts with the protein to form complex coacervates may be employed.
  • gum Arabic, sodium alginate, agar, carrageenan, carboxymethyl cellulose, sodium polyacrylate or polyphosphoric acid are suitable anionic polymers for the purpose of the invention. Both techniques are well known and largely described in the prior art, for instance by John C. Soper in "Utilization of Coacervated Flavors", Proceedings of Flavor Symposium; American Society, Chap. 10, 1995 .
  • the protein is an essential element of the process according to the invention, as it will go under gelation in order to form a wall around the oil droplets, before being hardened.
  • Use of proteins for encapsulation is limited but versatile, primarily due to their gelling and solubility characteristics. These characteristics are manipulated by changes in temperature, pH, addition of a second polyelectrolyte solution, a second solvent or even ionizing salt solution.
  • the molecular weight of the protein is typically of the order of 40000 to 100000.
  • the protein used in the process is chosen from group consisting of gelatin and albumin.
  • gelatin Preferably, one will use gelatin.
  • gelatin there is no particular limitation on the gelatin that can be used but it is preferable to use gelatin having good physicochemical and chemical properties as typified by good film forming ability, the nature of an ampholyte, the controllability of the quantity of charges by pH, and the occurrence of the change from solution to gel at a critical temperature.
  • any gelatin that satisfies the specification for use in the production of microcapsules may be employed. More preferably, a gelatin having an isoelectric point of 3.5 to10 and a bloom strength of 225 to 325 is used.
  • the core material to be encapsulated is a perfume or flavor ingredient or a perfume or flavor composition.
  • perfume and flavor ingredient or composition as used herein are deemed to define a variety of flavor and fragrance materials of both natural and synthetic origins. They include single compounds or mixture.
  • the process of the invention can provide in particular delivery system for hydrophobic volatile or labile components in liquid form. Specific examples of such components may be found in the current literature, e.g. in Fenaroli's Handbook of Flavor Ingredients, 1975, CRC Press ; Synthetic Food Adjuncts, 1947 by M.B. Jacobs, edited by Van Nostr and ; or Perfume and Flavor Chemicals by S.
  • Natural extracts can also be encapsulated into the system of the invention ; these include e.g., citrus extracts such as lemon, orange, lime, grapefruit or mandarin oils, or coffee, tea, mint, cocoa, vanilla or essential oils of herbs and spices, among others.
  • citrus extracts such as lemon, orange, lime, grapefruit or mandarin oils
  • coffee, tea, mint, cocoa, vanilla or essential oils of herbs and spices among others.
  • the proportions of hydrophobic ingredient or composition are comprised between 35 and 90% by weight relative to the weight of protein used.
  • the process of the invention is also suitable for the encapsulation of other core materials than perfuming or flavoring ingredients. It can be used for instance to prepare delivery systems for pharmaceuticals or cosmetic ingredients.
  • the emulsion or dispersion obtained under step a) is subjected to water dilution and/or pH adjustment to achieve coacervation.
  • the first two steps have to be carried out at a temperature above the gel point of the colloid material used.
  • the formed coacervate is further cooled to a temperature at or below the gel point of the protein to provide wall formation of microcapsules.
  • the temperature is between 5 and 15°C depending on the gelatin source.
  • the cooling rate is usually comprised between 0.25°/min and 1°/min.
  • the plant extract constituting the hardening agent is then added at a temperature between 15 and 30°C and a pH preferably between 3.5 and 7, and finally gentle agitation is provided for at least 48 h.
  • the plant extract components thus react with the protein wall and render it insoluble in water.
  • the delivery system obtainable by the above-described process is also a feature of the present invention.
  • Cross-linking of the protein to alter aqueous solubility is critical in encapsulation employing proteins.
  • the products obtained according to the present invention due to the novel cross-linking agent, show advantageous release characteristics compared with a classical coacervate cross-linked with glutaraldehyde as shown by the comparative example below.
  • microcapsules produced by the process of the invention can be used in many kinds of applications in the field of flavors and fragrances.
  • they can be used for the flavoring of baking applications, tobacco, frying and canning (thermal processing).
  • they can be used for the perfuming of varied consumer products such as household cleaners, premoistened wipes and personal care products. Therefore perfuming or flavoring compositions comprising microcapsules according to the invention together with other perfuming or flavoring co-ingredients, are also embodiments of the present invention.
  • Another embodiment of the invention relates to a method for insolubilizing proteins in water by adding a plant extract comprising substituted or unsubstituted phenolic compounds to a protein based coacervate.
  • Samples were stored at 40°C for 24 h and subsequently examined under microscope. These samples were tested for wall integrity by heating to 90°C for 15 min and examined under microscope.
  • Table 1 Coacervate stored at 40° for 24 h and heated at 90° for 15 min. Liquid smoke type Level [%] Observations 90°C - 15 min 40°C - 24h Charsol ® Supreme 0.28 Intact walls - Discrete particles Intact walls - Discrete particles Charsol ® Supreme 0.14 Intact walls - Walls fused Intact walls - Walls fused Charsol ® Supreme 0.07 Intact walls - Discrete particles Intact walls - Discrete particles Charoil ® Hichory 0.28 Intact walls - Discrete particles Intact walls - Discrete particles

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Abstract

L'invention concerne un procédé de préparation de microcapsules par coacervation, procédé selon lequel la réticulation d'une protéine est réalisée par un extrait végétal riche en composés phénoliques substitués ou non substitués.

Claims (18)

  1. Procédé pour la préparation de microcapsules comprenant un noyau de matériau hydrophobe, lequel procédé comprend les étapes consistant à:
    a) émulsifier ou disperser un liquide hydrophobe, un solide en suspension dans un liquide hydrophobe ou un solide dans une solution d'au moins une protéine de poids moléculaire élevé;
    b) soumettre l'émulsion ou la dispersion obtenue dans l'étape a) à une dilution aqueuse et/ou un ajustement de pH pour obtenir une coacervation;
    c) refroidir le coacervat formé à l'étape b) pour permettre la formation de la paroi des microcapsules;
    d) ajouter, à une température entre 15 et 30°C, un agent durcisseur au coacervat pour réticuler le mur formé; et
    e) agiter le mélange durant au moins 48 h pour achever la réaction de réticulation;
    caractérisé en ce que l'agent durcisseur utilisé à l'étape d) contient au moins un extrait de plante comprenant des composés phénoliques substitués ou non substitués.
  2. Procédé selon la revendication 1, caractérisé en ce que l'agent durcisseur représente de 0,5 à 2,5 % en poids par rapport au poids de la protéine, sur une base sèche.
  3. Procédé selon la revendication 1, caractérisé en ce que l'agent durcisseur contient au moins un extrait de plante sélectionné dans le groupe constitué d'extraits botaniques, d'extraits végétaux et d'extraits de bois.
  4. Procédé selon la revendication 3, caractérisé en ce que l'agent durcisseur contient un extrait de thé concentré.
  5. Procédé selon la revendication 3, caractérisé en ce que l'agent durcisseur contient de l'acide pyroligneux.
  6. Procédé selon la revendication 1, caractérisé en ce que le noyau de matériau hydrophobe est un ingrédient ou une composition parfumante ou aromatisante.
  7. Procédé selon la revendication 1, caractérisé en ce que la solution protéinique comprend en outre un polymère anionique.
  8. Procédé selon la revendication 7, caractérisé en ce que le polymère anionique est sélectionné dans le groupe constitué de gomme arabique, alginate de sodium, agar, carraghénane, carboxyméthylcellulose, polyacrylate de sodium ou acide polyphosphorique.
  9. Procédé selon la revendication 1, caractérisé en ce que la protéine est la gélatine.
  10. Microcapsules obtenues par un procédé selon la revendication 1.
  11. Microcapsules comprenant des murs gélifiés d'une protéine de haut poids moléculaire qui entourent au moins partiellement des noyaux de matériau hydrophobe, dans lesquelles les murs gélifiés sont réticulés au moyen d'un agent durcisseur contenant au moins un extrait de plante comprenant des composés phénoliques substitués ou non substitués.
  12. Microcapsules selon la revendication 11, caractérisées en ce que la protéine est la gélatine ou l'albumine et l'extrait de plante est sélectionné dans le groupe constitué d'extraits botaniques, d'extraits végétaux et d'extraits de bois.
  13. Méthode d'insolubilisation de protéines dans de l'eau, qui comprend l'ajout d'au moins un extrait de plante comprenant des composés phénoliques substitués ou non substitués à un coacervat à base de protéine pour former un mélange dans lequel l'extrait est présent dans une quantité suffisante pour durcir au moins une portion de la protéine du coacervat pour la rendre insoluble.
  14. Méthode pour conférer, améliorer ou modifier les propriétés organoleptiques d'une composition parfumante ou aromatisante, comprenant l'ajout à la composition de microcapsules selon la revendication 10.
  15. Composition parfumante ou article parfumé comprenant, outre les co-ingrédients parfumants, solvants ou adjuvants d'usage courant en parfumerie, des microcapsules selon la revendication 10.
  16. Article parfumé selon la revendication 15, sous la forme d'un nettoyant ménager, d'une lingette préimprégnée ou d'un produit de soins corporels.
  17. Composition aromatisante ou produit aromatisé comprenant, outre les co-ingrédients aromatisants, ou adjuvants d'usage courant dans l'industrie des arômes, des microcapsules selon la revendication 10.
  18. Produit aromatisé selon la revendication 17, sous la forme d'un produit de boulangerie, de tabac, de friture ou de conserve.
EP03787967A 2002-08-19 2003-08-12 Procede de preparation de microcapsules aromatiques ou parfumees Expired - Lifetime EP1531927B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US224441 1994-04-07
US10/224,441 US20040032036A1 (en) 2002-08-19 2002-08-19 Process for the preparation of flavor or fragrance microcapsules
PCT/IB2003/003612 WO2004016345A1 (fr) 2002-08-19 2003-08-12 Procede de preparation de microcapsules aromatiques ou parfumees

Publications (2)

Publication Number Publication Date
EP1531927A1 EP1531927A1 (fr) 2005-05-25
EP1531927B1 true EP1531927B1 (fr) 2008-12-03

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EP (1) EP1531927B1 (fr)
JP (1) JP2006511322A (fr)
CN (1) CN1330409C (fr)
AR (1) AR040979A1 (fr)
AT (1) ATE416029T1 (fr)
AU (1) AU2003253175A1 (fr)
BR (1) BR0313195A (fr)
DE (1) DE60325061D1 (fr)
ES (1) ES2316847T3 (fr)
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WO (1) WO2004016345A1 (fr)

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US9743688B2 (en) 2010-03-26 2017-08-29 Philip Morris Usa Inc. Emulsion/colloid mediated flavor encapsulation and delivery with tobacco-derived lipids
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ES2316847T3 (es) 2009-04-16
BR0313195A (pt) 2005-07-12
MXPA05001818A (es) 2005-08-16
CN1674978A (zh) 2005-09-28
ATE416029T1 (de) 2008-12-15
EP1531927A1 (fr) 2005-05-25
AR040979A1 (es) 2005-04-27
JP2006511322A (ja) 2006-04-06
CN1330409C (zh) 2007-08-08
US20050123757A1 (en) 2005-06-09
WO2004016345A1 (fr) 2004-02-26
DE60325061D1 (de) 2009-01-15
US20040032036A1 (en) 2004-02-19
AU2003253175A1 (en) 2004-03-03

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